Time and Time Again
by LiveLaughLove728
Summary: "For three thousand years it had been the same torturous cycle. The hero came, she fell in love, and he left. Over and over." We saw what happened with Leo after leaving Ogygia, but what about Calypso's side of things?


**Hello! I'm back again.**

 **For a while now I've been getting requests from you guys for a little Caleo, and I was bored earlier today and came across this little gem that had been sitting on my laptop since BoO first came out. I decided to dust it off and finish it up for you all today. I'm really happy with the end product and I hope you enjoy it!**

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Life was unfair. Calypso knew this already and had for quite some time, but that didn't make the pain any less unbearable. For three thousand years it had been the same torturous cycle. The hero came, she fell in love, and he left. Over and over. Odysseus. Abantes. Drake. Nicolaus. Percy.

Leo.

Leo, who was so much different. When he'd first shown up, a flaming, smoking projectile that had fallen from the sky and turned her dining table to kindling, she'd hated him. That had been a new experience for her. No hero she'd ever encountered on Ogygia had ever seemed so utterly unimpressive. He'd been so aggravating with the constant smoke and the metallic clanging, so withdrawn with his sarcasm and single-minded intent. She'd been so busy hating him and feeling bad for herself that she'd completely overlooked how amazing he actually was.

Leo was a different kind of hero, like none she'd ever met before. And that was almost worse.

 _We could start our own shop. Leo and Calypso's Garage: Auto Repair and Mechanical Monsters._ His words, so ridiculous at the time, echoed in her head now over and over again. She hadn't been able to bring herself to watch him sail away like she had for all her other heroes, though she knew by now he'd be little more than a speck on the horizon, if he was even still visible at all. She was alone again.

All the other times she'd seen it coming. She'd felt herself falling and knew what would happen. She'd been able to at least brace herself for the pain. This time, she hadn't. This time, her feet had been completely swept out from under her. Another week, he'd said, and her heart, against her will, had felt lighter. One more week. She'd have one more week with him.

And then, just like that, that gods-forsaken raft had washed ashore. She'd hidden her emotions well, but her heart had shattered at the sight of it. The time had come for Leo to leave and she was grossly unprepared. Still, she'd sprung to her feet and rushed to help him prepare the raft for his journey, fighting all the while against the tears that threatened to fall and grateful for the darkness to hide the few that did.

 _The raft finally got here._

 _You just noticed?_

 _But if it only shows up for guys you like—_

She'd interrupted him before he could finish that sentence, lying through her teeth, though it had made no difference. The raft was still there. The gods' curse couldn't be tricked just because she denied her feelings for him, even to herself. So she'd kissed him and then she'd run, because she'd had no other choice. If she'd stayed to watch another hero sail away, one who had stolen her heart in a way so completely different than any had before, she wasn't sure she'd have the will to go on.

A part of her, naïve even after all these centuries, almost wished he'd called after her. But that wouldn't happen; it couldn't, because that was how the curse worked. They could never stay.

She'd turned her back on Leo and stormed back up the beach, heartbroken and angry—not at Leo this time, but at the gods for cursing her, and at herself for supporting her father and deserving the curse to begin with. She made it as far as Leo's forge before she stopped, unable to go any further for fear she might actually shatter. She'd stood there, next to the place where they'd spent so much time. She had stayed that way until her knees grew week and she fell to the sand and allowed the tears to fall freely. It was easier to just embrace the pain and let it out; only then could healing begin.

She still hadn't moved.

It was hard to say how much time passed while she wallowed in misery beside the makeshift forge—a painful reminder of all she'd again lost. Eventually her eyes ran dry, but she remained on the ground, sand covering the legs of her jeans. _I'm coming back,_ he'd said, but they all said that, and they never did. They couldn't. And yet a part of her still wanted to believe him, still wanted to believe that Leo, who was different than any mortal hero she'd ever met, would be the first to keep his word.

But she couldn't hold him to it. In fact, she'd best just let him go completely. It was the only way she'd learned to keep going, by letting go and trying to forget.

She knew she needed to rid the island of reminders of him, to bury the memories. Numbly, she stood and retreated the rest of the way up the beach, past his camp and to her cave. She stripped off the shirt and jeans, and replaced them with one of her normal dresses. Her tied-back hair fell loose around her shoulders as she undid it and then wove it back into the customary braid she'd worn for the last hundred some years. She retrieved the clothes from the floor before her, gathered them in her arms and hesitated, staring down at them. Of course, standing motionless, even for a second, brought memories of the past days flooding back and she pain in her heart blazed anew. In a rush of anger, she threw the clothes as hard as she could into the fireplace. She had not seen the need to fireproof her own as she had Leo's, and the dwindling flames took to the light material instantly. Calypso watched the fabric burn as tears traced their way down her cheeks and knew that while she might soon regret destroying the sensible clothing she had become so fond of, her heart would thank her later. She'd learned long ago that holding onto reminders of loves lost did nothing to hasten the dulling of heartbreak's pain.

Bearing this in mind, she turned her back on the smoldering remains and strode purposefully back down the beach, to the forge. In her anger, she was of a mind to destroy every vestige of the thing, until it was just rubble in the sand, which would wash out to sea with the tides, but her resolve wavered when she reached the doorway.

If the memories had been painful before, here, in the very place where most of them had been born, they were downright torture. Images of Leo, hammering away on metal and fiddling with his Archimedes' sphere day and night flooded back. She remembered watching him from afar during her work in the garden and bringing him meals, talking to him, eventually joining in the work herself. She recalled him setting himself on fire on more than occasion, which had been disturbing at first, but later became nothing short of amusing once she knew he could not be harmed by such a thing. She remembered the way he spoke, playfully and yet hesitant, as if he were afraid of disapproval or reproof. She saw his hair in her mind's eye, brown, curly, and everywhere in the most adorable way. His eyes gleaming with laughter and mischief, and the way his mouth set when he was working hard on a project. She saw it all again and suddenly couldn't breathe. Her tears, which had dried some over the course of her march from the cave, flowed anew as hurt and rage at her circumstances faired inside her again. She stormed inside.

Leo hadn't left much behind, as most of the tools and materials he'd used had come from his tool belt and were returned then when he finished with them, but the surface of the makeshift workbench he'd built was still scattered with wood and metal scraps, pieces of cloth, the sail she'd woven for him to use on the raft they were building before the magical one finally showed up. All lay abandoned and unneeded now, which was exactly how she felt. With a distraught cry that would fall on deaf ears, Calypso reached out and violently swept all of it to the ground, where she then proceeded to kick at the pieces, ignoring the pain in her bare feet. She took the sail she'd crafted and, using every ounce of strength to do it, ripped it viciously in two. She pulled the wooden tabletop from the workbench and flung it out the doorway onto the beach, toppled the rest of it, and then, the anger still fueling her, crossed to a wall of the three-sided forge, built with the mud bricks Leo had crafted and heated himself, and pushed against it with all she had, ignoring the blood that soon sprouted from her fingertips. The structure was made well and was not willing to go down without a fight, but Calypso, with the Titan in her, was stronger than she looked and eventually one side of the joint bricks broke free from the other side and the wall fell with a crash, sending sand and ash flying up all around. Calypso fell with it and, the rough bricks scraping her exposed legs, landed atop the pile with a huff.

She sat dejectedly atop it for a moment, breathing heavily and cursing Leo for leaving behind so much work for her. Her anger had abated some in the wake of her temper tantrum and while her heart still ached excruciatingly, she was suddenly drained. Her eyes fell then on the makeshift bed that sat in the corner of the tiny camp. Little more than a handful of blankets atop the sand, it had served as a place for Leo to lay his head when he finally took a break from his endless hammering and slept. Silently, Calypso stood and walked over to it, picking her way between the debris of her own making that littered the ground. When she reached it, she lowered herself slowly down and spread out atop the covers, gathering them in her arms and burying her face in them. They still smelled like him.

She let go finally of the anger, and the pride, and the empty promises to herself that putting everything back to the way it was before her hero had ever crash landed in on the island would help her forget. She let go of every excuse she'd held since Leo had first left and allowed herself simply to cry. And cry she did, with everything in her, letting all of the pain, heartbreak, and longing bubble to the surface, to the forefront of her mind as she pictured his face and his smile and breathed in his sent, and she just cried.

She cried herself to sleep as the sun set, ushering in another lonely night on Ogygia, and when she awoke the next morning, she dragged herself up, squinting through swollen eyes, and left the ruined forge. She crossed the sand of the beach, where the sea sparkled under the rising sun of what would surely be a lovely morning, which would mock her misery with its beauty. When she arrived back at her cave, she bathed, tended to her injuries, dressed, and brushed her hair before pulling it back into its regular braid, grabbing her gardening tools, and heading out to mind the plants and visit the birds that had returned in Leo's absence, who were destined, it seemed, to be the only companions she'd ever be able to have.

The days turned into weeks, which blended together, as they always did on Calypso's island prison, into one endless stretch of lonely existence. She went about her days as she always had, tending her garden, singing with the birds, weaving and creating in her spare time, with only invisible magic servants to keep her company. She did not visit Leo's abandoned forge again, nor did she allow herself the luxury of shedding any more tears over him. She would, as she always did, learn to live again with the loss.

She allowed herself one luxury, however, and weaved herself another set of jeans and an accompanying white top like the ones she'd worn with him, as they truly did serve as practical apparel for one who crawled around in a garden all day. These clothes did, after all, come from her own hands and were technically completely separate from the ones she'd first made and later burned. Or so she told herself.

It was impossible to say how long it was that things went on like this. With no godly visitors to Ogygia and no news at all from the outside, Calypso was as alone and unaware as she'd ever been. Eventually, she fell into the same familiar rhythm she'd operated under over the centuries she spent stuck on her gods-forsaken island, and while the pain was still crippling when she allowed herself to dwell on it, she endured each day as it came.

Until the day that everything changed.

At first, she almost didn't believe it. She'd just finished tending her garden for the day and had gotten to her feet, tools in hand to be put away. She gazed out at the sea with no particular intent outside of simply admiring the beauty of it as the water sparkled blue under the noonday sun. It was a lovely day, as per usual on Ogygia. The sky was bright and dotted liberally with puffy white clouds, which alternately covered and revealed the sun, keeping the heat from becoming too much. For the moment, the sun was out and unobstructed in the sky, shining comfortably down on her. She studied the horizon, expecting nothing, and was unsurprised to find it bare. She was about to turn her back on the scene when she saw something sparkle from the corner of her eye. She turned and stared, far from shocked to see nothing there, and her heart, which had quickened for the smallest second, slowed again. She sighed, shaking her head at herself—and then froze.

Something glinted against the blue sky once more, clearly this time, and then did so again and again. Calypso watched as, before her very eyes, a golden speck in the distance circled closer and grew larger. She knew what it was before she could see it properly, but could only blink as the shape became unmistakably clear. A winged, golden dragon, flying toward her island. It couldn't be. And upon it's back, yelling and whooping for the whole world to hear, was…

She took off running, leaving her gardening tools to drop where they would in the dirt behind her.

Even as she watched, stopping just clear of the water's edge, Calypso wondered if she was dreaming; if the gods and the fates had not had enough yet and yearned to torture her further with scenes of love lost.

But even as the thought it, she knew this was no dream. Even if her tortured mind could conjure so perfect an image of her beloved hero atop a mount she never could have envisioned, no amount of imagination or god-altered apparition could so accurately portray the hero she loved as he whooped and cheered like a madman. It simply wasn't possible.

They came in for landing mere feet from her, but as she watched, the metal dragon, wings outstretched, stumbled as one of its legs gave out beneath it, and Leo—her Leo—was catapulted off it's back and flung face-first into the sand at her feet.

The dragon hobbled off, creaking painful sounds, and Leo braced himself on his forearms on the beach, sandy from head to toe. He did not notice her at first, due to the seaweed in his mouth, which he spat out, looking disgusted. Calypso watched, doing her best to remain stoic, even while her heart somersaulted in her chest and she barely refrained from shouting and jumping for joy, or simply weeping.

Finally, he looked up at her. Fighting with everything she had to keep a straight face, she informed him, "You're late." And yet, that he had returned at all was nothing short of a miracle; one which she would never have expected, despite his adamancy.

"Sorry, Sunshine," he replied, his voice and the pet name making her heart constrict in the best way, "Traffic was murder."

"You are covered with soot," she said, noticing for the first time the state of his apparel, "And you managed to ruin the clothes I made for you, which were impossible to ruin." And yet, here he lay, proof that anything was possible.

"Well, you know," he said, straightening until he knelt in the sand before her, "I'm all about doing the impossible." How closely his words echoed her thoughts very nearly made her smile. She offered her hand to him and helped him up. He stood before her, incredibly close, and appeared to drink her in, looking dazed as she'd ever seen him. If she was honest, she wasn't nearly much better.

She couldn't help but wrinkle her nose at the stench that registered now, like the scent of war—blood and sweat—mixed with the sea at low tide, and all severely burnt to a crisp. "You smell—"

"I know. Like I've been dead. Probably because I have been." He continued on, talking, as he always did, far too much. And she was interested in what he had to say, especially after that remark, but she wanted to kiss him far more. So she did, effectively silencing whatever else he had to say.

It was glorious. His heart slammed against hers and he kissed her back. She deepened it. What he obviously lacked in experience, he made up for in vigor, and she would have smiled at the thought that they would have plenty of time for him to improve, had she not been so engaged otherwise.

She let him go and waved vaguely, signaling her servants to pack for her everything she would need for the rest of her life. Two suitcases were deposited at her feet seconds later. Leo grinned at her. "Packed for a long trip, huh?"

"I don't plan on coming back." She glanced behind her at the cave that had been her home for so long, and was surprisingly unmoved at the idea of leaving it forever. She turned back to him. "Where will you take me, Leo?"

"Somewhere to fix my dragon. And then… wherever you want. How long was I gone, seriously?"

She had no idea. "Time is difficult on Ogygia. It felt like forever."

A series of emotions flashed across his face and he looked momentarily uncertain before his eyes settled on her once more. "So once you leave Ogygia, do you stay immortal or what?"

"I have no idea," she told him honestly. She found she didn't much care either way.

"And you're okay with that?"

"More than okay."

"Well then!" he said excitedly, turning and summoning his dragon friend to them.

Calypso felt the need to voice her thoughts. "So we take off with no plan. No idea where we'll go or what problems await beyond this island. Many questions and no tidy answers?" She found herself looking forward to the idea far more than she let on.

Leo upturned his palms in a carefree gesture. "That's how I fly, Sunshine. Can I get your bags?"

Calypso could not remember the last time she'd felt so light; the last time her life had seemed so full of possibility. For so long, she'd merely existed, enduring an eternity of torturous limbo and loss. Again and again she'd fallen in love and watched that love choose other things before her. Again and again she'd been left alone and broken. For so long she'd wanted nothing more than to be freed of her misery, to finally be released, even if it meant death. And now, for the first time, she was truly receiving the opportunity to live.

She stared into Leo's deep brown eyes, so full of life and love and possibility, and she thought, impossibly, that maybe it had all been worth it to get her where she was right now. To be in love and free, and leaving that wretched half-life behind.

Calypso smiled. "Absolutely."

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